Vacation Rentals in Chalk Hill Estate Vineyard, CA: Compare 10+ Sites & Save

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  6.  Chalk Hill Estate Vineyard

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162 Best Vacation Rentals in Chalk Hill Estate Vineyard (Starting from $128)

Chalk Hill Cottage - 1 BR w/ Sleeper Sofa
Chalk Hill Cottage - 1 BR w/ Sleeper Sofa
House
Chalk Hill Estate Vineyard, Healdsburg, California, USA
1.1k from Chalk Hill Estate Vineyard center

Parking, Internet, Kitchen, Air Conditioner, Pet Friendly, Child Friendly

1 Bedroom4 Guests
New to Booking
$128
Average price / night
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Exceptional Estate Vineyards in Healdsburg Sonoma County
Exceptional Estate Vineyards in Healdsburg Sonoma County
Villa
Healdsburg, CA, 95448, United States
0.9k from Chalk Hill Estate Vineyard center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
9.4

Superb

3 reviews

$1489
Average price / night
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Peaceful Windsor Retreat with Private Hot Tub!
Peaceful Windsor Retreat with Private Hot Tub!
House
Windsor, CA, USA
4.1k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

3 Bedrooms8 Guests
9.5

Superb

2 reviews

$417
Average price / night
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Chalk Hill Cottage Close to Wineries
Chalk Hill Cottage Close to Wineries
Cottage
Healdsburg, CA, 95448, United States
1.1k from Chalk Hill Estate Vineyard center

AC, Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
9.8

Exceptional

48 reviews

$275
Average price / night
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Leslie Creek House
Leslie Creek House
House
Mark West Springs, CA, USA
4.7k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

4 Bedrooms8 Guests
8.5

Very Good

2 reviews

$271
Average price / night
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Modern Hilltop Healdsburg Residence With 360' Views
Modern Hilltop Healdsburg Residence With 360' Views
House
Healdsburg, CA, 95448, United States
1.7k from Chalk Hill Estate Vineyard center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

38 reviews

$2888
Average price / night
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Wine County Retreat
Wine County Retreat
House
Windsor, CA, USA
4.8k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$533
Average price / night
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Wine Country Get Away
Wine Country Get Away
House
Windsor, CA, 95492, United States
1.9k from Chalk Hill Estate Vineyard center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
9.8

Exceptional

34 reviews

$232
Average price / night
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Brand New Listing – Windsor “Winetopia” Getaway
Brand New Listing – Windsor “Winetopia” Getaway
House
Windsor, CA, USA
5.1k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$437
Average price / night
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Wine Country Estate Home
Wine Country Estate Home
House
Santa Rosa, CA, 95403, United States
2.5k from Chalk Hill Estate Vineyard center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Kitchen, Laundry

4 Bedrooms8 Guests
9.0

Fabulous

7 reviews

$1142
Average price / night
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Healdsburg Winemaker's Home
Healdsburg Winemaker's Home
House
Windsor, CA, USA
5.3k from Chalk Hill Estate Vineyard center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

6 Bedrooms8 Guests
New to Booking
$585
Average price / night
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Peaceful Healdsburg Wine Country Retreat with Vineyard Views
Peaceful Healdsburg Wine Country Retreat with Vineyard Views
House
Healdsburg, CA, 95448, United States
2.6k from Chalk Hill Estate Vineyard center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$447
Average price / night
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The Dragonfly- Complimentary Wine Tasting At Croix Included!
The Dragonfly- Complimentary Wine Tasting At Croix Included!
House
Healdsburg, CA, USA
5.4k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$810
Average price / night
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Peaceful 4 Bed 2 Bath Home with Spacious Backyard
Peaceful 4 Bed 2 Bath Home with Spacious Backyard
House
Windsor, CA, 95492, United States
2.6k from Chalk Hill Estate Vineyard center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.4

Superb

12 reviews

$201
Average price / night
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Gable by AvantStay Beautiful 3.5 Acre Oasis w Gorgeous Views Pool Hot Tub
Gable by AvantStay Beautiful 3.5 Acre Oasis w Gorgeous Views Pool Hot Tub
House
Santa Rosa, CA, USA
5.5k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

5 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$1325
Average price / night
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SUNNY SPACIOUS RETREAT NEAR GOLF COURSE W/ HOT TUB - WINE COUNTRY GETAWAY
SUNNY SPACIOUS RETREAT NEAR GOLF COURSE W/ HOT TUB - WINE COUNTRY GETAWAY
House
Windsor, CA, 95492, United States
2.7k from Chalk Hill Estate Vineyard center

AC, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave

4 Bedrooms8 Guests
7.4

Good

3 reviews

$244
Average price / night
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Serenity On Dragonfly A Wine Country Escape
Serenity On Dragonfly A Wine Country Escape
House
Healdsburg, CA, USA
5.5k from Chalk Hill Estate Vineyard center

Barbecue/Outdoor Cooking, Security/Safety, Sports/Activities, Wellness Facilities, Internet, Spa, Fireplace/Heating

3 Bedrooms8 Guests
New to Booking
$861
Average price / night
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Luxury Sonoma County wine country retreat just 10 minutes from Healdsburg.
Luxury Sonoma County wine country retreat just 10 minutes from Healdsburg.
House
Windsor, CA, 95492, United States
2.8k from Chalk Hill Estate Vineyard center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1512
Average price / night
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Herb Retreat
Herb Retreat
House
Windsor, CA, USA
5.5k from Chalk Hill Estate Vineyard center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1241
Average price / night
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Sonoma Valley - Hot Tub, Pool, BBQ & Gym
Sonoma Valley - Hot Tub, Pool, BBQ & Gym
House
Santa Rosa, CA, 95404, United States
3.5k from Chalk Hill Estate Vineyard center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1399
Average price / night
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Modern Santa Rosa Retreat Near Wineries & Trails
Modern Santa Rosa Retreat Near Wineries & Trails
House
Santa Rosa, CA, 95403, United States
3.5k from Chalk Hill Estate Vineyard center

AC, Fireplace, Free Parking, Internet, Kitchen, Laundry, No Smoking, Patio, TV

4 Bedrooms8 Guests
New to Booking
$1350
Average price / night
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'Villa Moderna' Ultimate Wine Country Estate. .WITH POOL
'Villa Moderna' Ultimate Wine Country Estate. .WITH POOL
House
Santa Rosa, CA, 95403, United States
3.5k from Chalk Hill Estate Vineyard center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$2009
Average price / night
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Secluded 4BDR Retreat w/ Pool, Hot Tub, Views | Shiloh Vista Estate by AvantStay
Secluded 4BDR Retreat w/ Pool, Hot Tub, Views | Shiloh Vista Estate by AvantStay
House
Santa Rosa, CA, 95403, United States
3.6k from Chalk Hill Estate Vineyard center

AC, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

4 Bedrooms10 Guests
New to Booking
$1645
Average price / night
Check Availability
Wine Country Getaway W/ Fire Pit & Hot Tub!
Wine Country Getaway W/ Fire Pit & Hot Tub!
House
Windsor, CA, 95492, United States
3.7k from Chalk Hill Estate Vineyard center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

26 reviews

$745
Average price / night
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Peaceful Windsor Retreat w/ Private Hot Tub!
Peaceful Windsor Retreat w/ Private Hot Tub!
House
Windsor, CA, 95492, United States
4.1k from Chalk Hill Estate Vineyard center

AC, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$552
Average price / night
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Luxury Private Pool Home near Healdsburg
Luxury Private Pool Home near Healdsburg
House
Windsor, CA, 95492, United States
4.2k from Chalk Hill Estate Vineyard center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$472
Average price / night
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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
House
Healdsburg, CA, 95448, United States
4.4k from Chalk Hill Estate Vineyard center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

6 Bedrooms12 Guests
9.2

Superb

39 reviews

$1601
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Chalk Hill Estate Vineyard.

Where to stay in Chalk Hill Estate Vineyard? Best neighborhoods & areas

Chalk Hill Estate Vineyard Vacation Rentals on the Map

Frequently Asked Questions

You can explore 162 verified vacation rentals in Chalk Hill Estate Vineyard. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Chalk Hill Estate Vineyard vary depending on the season, property size, and location. Rates typically start from around $128 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Chalk Hill Estate Vineyard include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Chalk Hill Estate Vineyard welcome pets. Currently, 28 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Chalk Hill Estate Vineyard often include amenities such as Fireplace/Heating, Wellness Facilities, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.